


Each Night Begins a New Day

by Fallynleaf



Category: Supernatural
Genre: Character Study, Dean Has a Cowboy Kink, Dean in Panties, First Time, M/M, Magic Made Them Do It, Porn With Plot
Language: English
Status: Completed
Published: 2017-02-16
Updated: 2017-02-16
Packaged: 2018-09-24 20:12:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,610
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9784268
Author URL: https://archiveofourown.org/users/Fallynleaf/pseuds/Fallynleaf
Summary: The working title for this fic was:"a character study through porn"





	

**Author's Note:**

> I started writing this fic in 2015, but just could not figure out how I wanted to end it. Since then, I've rewritten the ending six different times. I'm still not completely satisfied with it, but I wanted to finally finish it, so I decided to post it today in honor of International Fanworks Day.
> 
> This is a PWP fic that could have a bibliography. I can cite no less than three different episodes for why I wrote Dean's kinks this way. It started as an attempt to combine them, and then, well, it got a bit out of hand from there.
> 
> The title is from the song "Mammas Don't Let Your Babies Grow Up to Be Cowboys."

As he stood outside the bathroom door, staring at the thin sliver of light underneath it, Sam knew that they were fucked.

"Dean..." he started. Then he stopped, because there was really nothing he could say after that.

"You're not supposed to be here," Dean said, his voice coming from behind the door. "Fuck, Sam..."

"I know."

"I hate witches. I fucking _hate_ them. This is so goddamn _invasive_ ," Dean said.

"Yeah, well, that's what you get when you combine djinn magic and sex spells," Sam said. Usually it helped, knowing what you're up against. Today, it just made everything worse, because there was no pretending that this wasn't exactly what it was.

No pretending that they weren't both trapped in Dean's deepest sex fantasy, with Sam cast as the major supporting role.

"I don't even know how to, y'know, properly fuck another guy," Sam said, just making conversation while he waited. "Have you ever done it before?" he asked.

"No." Dean's answer was quick, a little rough.

"Are you even into guys?" Sam asked.

Silence. And that was really as much of an answer as Sam needed.

"I didn't know that," Sam said quietly. But then again, maybe that was part of the whole _deepest sex fantasy_ for Dean. That he wanted to fuck a guy, but never could come to terms with that desire enough to actually realize it. "And the whole incest thing?" Sam asked, quieter.

"No!" Dean said. "I'm not‒ that's not‒ I've never thought of you like that, Sammy," he said firmly.

Sam started to wonder if there was any chance that could also be an even deeper part of the whole _deepest sex fantasy_ , but he decided to end that thought before it took him somewhere he really didn't want to go. It was bad enough that he had to fuck his brother; he really didn't want to discover that said brother had latent incestuous feelings that neither of them had previously known about.

"I have to say, this is the absolute most bland motel room I've ever seen in my life," Sam said, glancing around them. It was a slightly safer topic.

"That's cause the place doesn't matter to me," Dean said. "I don't get off on nice drapery."

That wasn't actually surprising, Sam realized. Dean had never been particularly picky about _where_ he had sex. As long as the location was convenient for his purposes, he'd use it. And motel rooms were private, impersonal, and kind of ideal for random hookups. Plus, for Dean, they probably felt familiar. Safe.

"I guess I'm about to find out what you do get off on, then," Sam said, sighing. "As soon as you leave the bathroom. Which, c'mon, Dean! Let's just get this over with!"

"We could just try waiting it out," Dean suggested.

"No. If djinn magic is involved, we’re probably comatose back in the real world. And I don't know how long we can survive like that. We need to just... finish this and get out, and then never talk about it again."

Dean was silent. And Sam was finding himself growing more and more frustrated. "Dean!" he said. "If you don't come out in five minutes, I'm going to bust down the door!"

"Fine!" Dean shouted. "Just... don't look at me, okay?"

"I can't not look at you! Unless blindfolds are part of this fucked up sex fantasy," Sam said.

The door opened.

Sam turned around just in time to see Dean step out, and then both of them froze.

"Holy shit," Sam said.

"Holy shit," Dean said at the same time.

Sam couldn't take his eyes off of Dean. Because Dean was wearing pink satin panties and a matching bra. And he wore mascara and eye shadow. And, judging by the shine and color on his lips, he had lip gloss on, too.

"Uh..." Sam's brain was flatlining.

At some point, he realized that Dean was staring at him, too, and that was when he bothered to glance down and see what had provoked that reaction.

Cowboy boots. He was wearing cowboy boots. And a belt with a large buckle. And there was something on his head that had about the same weight and feel as a cowboy hat.

"Your fucking western fetish," Sam said. "How did I forget," he said flatly.

Dean opened his mouth, then closed it, then opened it again. He kind of shrank back a little, like he was trying to hide the fact that he was dressed in _women's lingerie and makeup_. Which, _holy shit_ was still Sam's reaction.

The worst part was that looking at Dean dressed like that had Sam half-hard. He'd wondered if getting it up was going to be a problem, but apparently not. Either the sex-wish magic had that one covered, or Sam had an incestuous crossdressing kink that he really didn't want to know that he had.

And there wasn't really any possible way for Dean to hide that he was getting hard, too. Sam's eyes just kept drifting to those damn panties.

"So..." Sam said, his voice uneven. "How does the rest of this sex fantasy go?"

Dean mumbled something.

"What?" Sam asked.

"I said, you need to‒ to take‒" Dean stumbled over the words, and the last part of his sentence, Sam could barely make out. "You need to take control," Dean gritted out. He wouldn't look at Sam. Just cast his eyes demurely on the floor.

"Oh," Sam said. And then he _got_ it. " _Oh_. You want _me_ , the manly cowboy, to take you and shove you up against the wall and fuck some masculinity into your feminine ass."

Dean nodded miserably. Sam marveled that all it took to strip away decades of built-up false confidence was a couple pieces of lingerie.

"Hey, it's okay," Sam said. "I already knew that your ultimate sex fantasy would feature some sort of gendered bullshit‒" he just didn't know that Dean would put himself on the feminine side of it. "‒It makes sense, the way we were raised." He sighed. "And being like a woman probably feels _wrong_ and _bad_ and _naughty_ , so of course you'd get off on it."

"Sam," Dean grit out. "Less psychoanalyzing and more anal...izing."

Sam looked at him with an expression that just said: _really?_ Dean kind of half shrugged in response.

"Okay," Sam said. "Let's just get this over with."

He took a step closer to Dean, and Dean tensed. Sam waited as Dean forced himself to relax, and then he took another step, and then another, and then he was standing right in front of Dean, close enough to see the shimmer of his eye shadow, to see how full Dean's lips looked with color and gloss on them.

"Did you put it on?" Sam asked, his voice quiet, almost reverent.

"No. It kind of just appeared on me with the costume," Dean said. His gaze flicked between Sam's eyes and his lips.

Sam reached up and grasped Dean's face gently in his hand. He smoothed his thumb over Dean's skin without thinking, and Dean's eyes fluttered closed. For a moment, the two of them just stood there like that, unmoving.

Dean's eyes opened.

Then Sam leaned down, and Dean leaned up, and their lips were pressing together. For the first half-second, Sam couldn't shake the feeling that he was kissing his brother, and everything felt weird.

And then Dean's lips parted.

After that, it was... good. _Really_ good. Dean was the tallest person that Sam had ever kissed, and Sam barely had to bend his neck to reach him. The lip gloss made Dean's lips feel soft and girly, and that helped make it familiar without feeling _too_ familiar.

But the way Dean moved, the way he kissed, that was all Sam's brother.

And Sam was maybe starting to realize that he really actually didn't mind kissing his brother. At all. He kind of wished they could just keep doing it for a while. It felt good, and he _knew_ Dean, and Dean knew _him_.

He didn't think that standing here and just kissing Dean would miraculously solve all of their problems, though. So he decided he'd keep to his word on the whole _shove you up against the wall_ thing.

From the sound Dean made as soon as his back hit the wall, it sounded like Sam had made the right decision.

Sam pressed in closer to Dean. He moved so that their bodies were almost flush against each other, and then _oh_. That was what it felt like when his very hard cock pressed against Dean's also hard cock. Sam ground his hips experimentally.

"Sam," Dean said, his voice ragged.

Sam responded by rubbing against him some more. It felt good, but he imagined it might feel even better if their clothes weren't in the way.

"The bed," Sam said, stepping back. Dean stared at him, then slowly walked over to the bed. He sat down at the end of it.

The large belt buckle made a lot of sound as Sam started to undo it. He walked over to stand in front of Dean at the end of the bed. After he undid his belt, he left it loose but didn't pull it out of the belt loops, assuming that Dean probably wanted him to keep as much of the ridiculous western clothes on as possible.

Then Sam unzipped the front of his jeans. He looked up and found Dean watching him silently.

Sam held Dean's gaze as he hooked his fingers in his underwear and pulled them down along with his jeans.

Then Dean dropped his eyes to look, and in the same moment, Sam leaned over and gently pushed Dean down onto his back on the bed.

"Is this okay?" Sam asked.

Dean nodded. "Yeah," he said.

Sam was honestly a little surprised how quiet Dean had been the whole time. He'd pegged Dean for a dirty-talker, or at least someone who moaned and made porn noises during sex, but there had been none of that. Maybe Dean was too nervous. Or maybe, deep down, he actually didn't really want to be having that kind of sex after all.

Sam looked down at Dean, and then all of a sudden he didn't know what he was doing. He just stood there with his pants open, staring dumbly.

And Dean just reached up and grabbed Sam's hand, placing it on the elastic of the panties.

Sam ran his hands along the elastic, feeling the texture of the lace. His hand was inches away from Dean's dick, but that didn't really bother him, because he was really turned on, and Dean was turned on, and Sam knew that it was because of him. He ran his fingers over the satin down the bulge, and Dean started to squirm and buck his hips into Sam's touch.

Then Sam reached around and grasped the elastic on both sides of Dean's hips and said: "Lift."

Dean did, and Sam slipped the panties barely off so that they stretched over Dean's thighs instead of his hips, baring everything: his dick, his balls, his asshole.

"I think I'm already prepped, so for the love of god, please just stick it in me, Sam," Dean said.

"Uh..." Sam looked at the glisten of lube inside Dean's ass, and he still didn't know exactly how anal sex worked, but he hoped that the magic also maybe stretched Dean out a little, because he really wasn't sure that his dick could fit inside there. He also hoped that the way they were currently positioned was a good angle for entry, because he really didn't want to waddle around the room with his pants around his ankles to find another way to do this.

He stepped forward so that the backs of Dean's thighs were pressing against him, and then he grasped his cock and placed the head against Dean's asshole. He gave an experimental thrust.

And Sam realized that his worry that the two of them wouldn't fit together was never going to be a problem.

Because it was perfect. The pressure around Sam's cock, the way that the two of them shifted and immediately found a rhythm together, the knowledge that this was _Dean_ wrapped around him, that in this moment, they were almost occupying the same space.

Sam looked down and his eyes met Dean's and stayed there. Dean's eyes were shining, his expression soft and trusting. This was clearly the most vulnerable he had ever felt in his life, and he and Sam both knew it.

It didn't matter how long the actual sex lasted. At some point, Sam reached down to stroke Dean's cock, and after that, it wasn't long before Dean came with a strangled cry of "Sammy!" and Sam followed him shortly after that.

Dean was crying when Sam pulled out.

Sam just flopped onto the bed beside him and waited it out. He didn't say anything. He felt somewhere between utterly exhausted and blissed out, and he knew that whatever he was feeling, it had to be at least ten times worse for Dean.

After some time, Dean spoke, his voice rough. "That was the best and the worst orgasm of my entire life.

"Yeah, I'll say," Sam said. He blinked up at the ceiling. "I wonder when we're going to wake up back in the real world?"

Dean was quiet. "I'm not sure that it's over yet," he said.

"Dude, there is no way I have the energy for round two," Sam said flatly. He didn't care if Dean teased him for his lack of stamina; he felt completely drained.

"No, I think... I want‒" Dean took a breath. "To go to sleep. With you."

"Oh." Sam turned to look at him. "Okay."

He sat up and immediately remembered that he still had all of the stupid clothes on. Well, except for the cowboy hat, since he'd swept it off of his head before he'd attempted to lay down.

He pulled up his underwear and pants so that he could take off the boots, but they proved harder to remove than he'd thought, so he sat and tugged at them for a minute before they were loose enough to kick off. "These boots are annoying," he said.

"They're hot, though," Dean said, his voice falsely casual. And Sam was about to agree about the warmth before he realized that Dean was telling him that he thought Sam looked attractive in them.

"I don't know if that's worth it," Sam said, after a little deliberation. He unbuttoned his shirt and then shrugged it off, discarding it on the floor with the boots.

He hesitated a little after he shoved the jeans back down and stepped out of them, unsure if he should remove his underwear for this, too, but then he looked over at Dean and realized that Dean had the choice of either sleeping in satin lingerie or sleeping naked, and Sam didn't want to have the unfair advantage over him, so he decided to ditch the underwear.

Sam ended up helping Dean unclasp the bra, since neither of them had ever had to unhook their own bra before, and Dean's fingers were fumbling with the clasp.

 And then they were both naked and somehow not smeared with bodily fluids, and Dean's makeup had disappeared somewhere in the process, too. This _perfect sex fantasy_ magic was damn inconsistent, Sam thought. It let them avoid the cleanup and prep, but none of the nerves and awkward steps in between.

Dean pulled back the covers on one side of the bed and crawled into it. Sam joined him right after. He maintained a bit of space between them at first, not knowing exactly what Dean wanted.

Dean tossed and turned a bit, seeming restless. He finally turned towards Sam, and said: "Sammy, just‒ come here."

And that's when Sam realized that Dean wanted to cuddle. He wanted a manly cowboy to order him around and fuck him in satin panties, and then he wanted to strip away all of the gendered bullshit and just fall asleep with someone holding him.

So Sam scooted closer and reached out and pulled Dean towards him. Dean ended up tucked under Sam's chin, and Sam knew that if this was any other occasion, Dean would've protested loudly and refused to let Sam be the big spoon, even if he was the one craving the comfort at the moment, but even Dean knew better than to try and lie about what he wanted right now.

"This sucks," Dean mumbled into Sam.

"I know," Sam said.

They just lay there together, breathing softly, but neither of them were quite on the verge of sleep.

"I gotta say, when I first saw the costumes, I thought there'd be more roleplay," Sam admitted to Dean.

"It's too fake," Dean explained.

"And the costumes weren't?" Sam said.

Dean was silent for a minute. When he finally spoke, his voice was carefully even. "I can't lie to you, Sam. Never have been able to. I've been trying my whole damn life, and you always see right through me." Dean sighed. "Plus, roleplay's not hot. It's too close to what we do for work."

"Yeah..." Sam said, agreeing with the last part, but not addressing any of the rest of it.

He snuggled a little closer to Dean, just because he could.

"I love you," Sam said. "I know we don't say it, but I want to make sure you know."

Dean didn't respond right away. "I love you too, Sammy," he said. "Always have, always will." He didn't even try and diffuse the confession by calling Sam a girl. But maybe that was because Dean wasn't really in a position to make that accusation, since he had just been in women's lingerie and makeup not even a half hour ago. Regardless, Sam was grateful.

It took a while before either of them fell asleep. Neither of them really had anything more to say, but the motel room was unusually quiet, with no outside sounds besides the usual ambient room noise.

And Sam realized that he kind of felt... at peace. There was nothing left to do besides wait, and then he and Dean would wake up and have to figure out what the hell their relationship even was now, but until then, they could just lay here and sleep and not worry that anything was going to attack them.

Sam fell asleep sometime after Dean did.

Then he woke up and realized that they were still in bed together and not back in the real world like they should be.

 _Did I do something wrong?_ Sam wondered, looking at Dean's sleeping face.

Then Dean's breathing pattern changed. His arms tensed a little as he came awake, but he didn't move and he didn't open his eyes yet.

"We're still trapped here," Sam told him.

"I know. Not for much longer, though," Dean said. He absently stroked Sam's back, his fingers warm against Sam's skin.

"Why?" Sam asked.

"Because..." Dean let out a slow breath. "I needed to wake up and be sure that you're still here."

Sam felt something like guilt, at that. But not regret. Not even after everything that had happened. "I won't leave you again, Dean," he said. It was both a statement and a promise.

Dean's eyes opened. He looked at Sam, and Sam looked at him.

And that's when Sam woke up for real.

He felt hard floor underneath him, his head pounding with a dizzy ache. A couple feet away, he heard the sound of Dean waking up, too. A groan and a couple muttered curses.

After Sam managed to sit up and gaze blearily around him, he realized that they were the only people still in the room. "Hey, the witch is gone," Sam said.

"Dammit!" Dean roared. "I'm going to‒" he started to list exactly how he would like to kill her, but Sam tuned him out.

"Dean, I think we scared her enough," Sam said, cutting him off. "I think she's probably going to stop doing spells. And if she doesn't... then we'll just track her down again and make her put a stop to it."

"I want to see _her_ have to experience her deepest perfect sex fantasy," Dean said. "I want to‒" He stood there with his hands curled tight into fists, and he clearly really wanted to punch something, but there was nothing around for him to take it out on.

So Sam just watched and waited as the wounded fury slowly faded out of Dean. And then it was just the two of them standing in the room, not quite looking each other in the eye.

They walked back to the Impala and climbed into it without a word. Dean started the car, and they were on the road again. Another job done, another city in the rear view mirror.

 

* * *

 

They didn't talk about it.

There wasn't really much to say, honestly. And even if there was, this wasn't a conversation that either one of them wanted to have in the car. Sam felt comfortable with the silence, with the familiar hum of the car's engine, and the classic rock in the tape deck.

When they pulled up at a motel, Sam half expected Dean to ask for another room, or immediately take off in an attempt to put some space between him and Sam, but he didn't. He just propped himself up on the far bed and started cleaning a gun.

Sam sat at the little uneven table at the opposite side of the room, laptop in front of him, his feet stretched out and tangled with the legs of the other chair in the cramped space beneath the table. He was searching for another case, but his eyes kept trying to wander, and he couldn't stay focused.

So he let his eyes wander, and they took him to Dean.

Dean looked over at Sam, too. They stared at each other, but it was softer than that. More of a _gaze_ then a _stare_. Normally, Sam wouldn't just gaze unabashedly at Dean like this, because it would be weird, but after everything that had just happened, it didn't actually feel that weird.

It felt... inevitable, maybe. Like they'd been heading here the whole time and just didn't know it.

"Probably should've figured it out sooner," Sam said.

"Figured out what?" Dean asked.

Sam took a breath. "That you're it for me," he said.

Dean set down the gun and leaned back a bit. "Yeah..." he said.

It was a comfortable realization. Like coming home. Sam closed his laptop and pushed his chair back, then stood up.

He walked over towards Dean, then sat across from him on the other bed.

"What are you doing?" Dean asked.

Sam shrugged.

"I'm sorry, Sam." Dean sighed.

Sam frowned. "Sorry for what?"

Dean picked up the gun again. He resumed cleaning it, resolutely not looking at Sam. "For messing us up. For messing _you_ up."

"Hey, you can't take all the blame for this one," Sam said. "You think it'd have been any different if it was _my_ dream?"

"It'd be you and Jess fucking in your suburban room with all of your law degrees hung on the walls and your 2.1 kids asleep in the next room over," Dean said flatly. "And I wouldn't be there."

"And who did you think would be in _your_ dream, Dean? Cassie? Lisa? Some other old flame that you've never mentioned? But you know what? You never know what you actually want until you get it." Sam exhaled an angry sigh and stood up. " _Fuck_ , Dean. Did you think you were the only one who was into guys?"

"What?"

It wasn't exactly the way Sam had planned on coming out to his brother, but then again, that was probably how Dean felt about how _he'd_ came out, so it was only fair.

"But you said you've never done it," Dean said.

"That doesn't mean I've never wanted to," Sam said. "I just... it's so much easier to meet girls than guys, and living with you and dad made it even harder. I thought I'd maybe try it in college, but then I met Jess, and, well..." Sam must've looked sufficiently miserable, because the sudden anger in the room seemed to fade.

"So I was your first, then?" Dean said.

"If we're counting dream sex, then no," Sam said, his voice flat. He sat back down again.

A long moment of quiet passed. Sam was staring at the floor, his eyes unfocused, watching passing headlights dance across the stained carpet.

And then Dean said, "I didn't think they meant anything." He expelled a breath. "The dreams, y'know. With men in cowboy boots."

Sam snorted. "You're too good at repressing things," he said. "But then, I guess we both are."

"So, does this mean we've talked about it now, and never have to mention any of it ever again?" Dean said.

"As long as you understand that this isn't on you," Sam said. "I liked it, too."

Dean didn't respond. So Sam added: "If you want, next time I'll be on the bottom."

"Next time we get trapped in a sex fantasy?" Dean said, incredulous.

Sam shrugged. "Or another time," he said.

"Sam..." Dean said. He could put so many emotions into just that one word, and sometimes it seemed like that was the only time that Dean allowed himself to show them. Just one syllable, and he was stripped bare.

"How many times do I have to confess before you'll believe it?" Sam said.

Dean looked up at him. For a long moment, they just stared at each other, breathing gently, two worn-out men in another worn-out motel.

Sam reached out towards Dean, but paused before his hand touched Dean’s face. Dean closed his eyes, briefly. When he opened them, Sam leaned in, and Dean moved towards him, and then they were kissing.

It didn’t last long. Sam pulled back after a couple seconds, and Dean tried to follow him at first, then eased back.

“If we do this, I can’t be the one initiating everything,” Sam said. “I have to know that you want it, too. That you’re not just doing it for me.”

Dean responded by closing the distance between their beds and kissing him. It was a rough kiss that quickly became soft. They stood up, and Sam, not knowing exactly what to do with his hands, wrapped them around Dean, and Dean’s hands fell away from Sam’s face as he moved to kiss Sam’s neck, and then they were both just holding each other, pulling the other so close that it went from being a kiss to being an embrace.

Sam didn’t know how long they stayed like that. They clung to each other like they were drowning.

Finally, Dean’s arms begin to loosen, and Sam let go of him, and then they stepped apart.

Dean chuckled weakly, and then Sam started, too, and they both laughed quietly for a minute.

“This is so fucked,” Dean said. But even as he spoke, he was leaning towards Sam. And Sam mumbled “Yeah” right as their lips met.

That night, they only went as far as kissing. But afterward, Sam crawled into Dean’s bed, and Dean slung an arm over him, and when Sam woke up, Dean was stretched out beside him, one arm flung wide, the other tucked beside Sam, and Dean was smiling before he even opened his eyes.


End file.
